A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check availability on Pittsfield Pet-friendly Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Pittsfield pet-friendly hotels

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A multi-story hotel with a brick facade and a flat roof.
A pool area with a glass ceiling, multiple levels, and outdoor seating.
A lobby with three grey armchairs, a small round table with a plant, and a patterned rug.

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Nicole
₩162,408
₩181,415 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Jermaine
₩157,990
₩176,475 total
includes taxes & fees
Sep 20 - Sep 21
Best Western Plus Berkshire Hills Inn & Suites
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ken
₩162,408
₩181,415 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A building entrance with a large planter with purple flowers and a small tree.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A library with bookshelves, a television, and two armchairs.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

4. Hotel On North

Hotel On North
Pittsfield
United States
Drew
₩246,365
₩275,190 total
includes taxes & fees
Sep 7 - Sep 8
Hotel On North
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A compact living space with a kitchenette, a dining area, and a sofa.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

5. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
₩136,258
₩152,196 total
includes taxes & fees
Sep 1 - Sep 2
The Central Downtown Inn & Suites
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

6. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
₩203,863
₩227,715 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Lenox Pittsfield
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
₩169,671
₩189,521 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn & Suites Berkshires-Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

8. Berkshires Untold

Berkshires Untold
Lenox
United States
Christine
₩192,594
₩215,128 total
includes taxes & fees
Sep 28 - Sep 29
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lodge with a large building and a dock by a lake, surrounded by forest.
A dining area with large windows, wooden furniture, and a view of a lake.

9. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
James
₩175,483
₩196,014 total
includes taxes & fees
Sep 21 - Sep 22
The Black Swan Lee - Lenox, an Ascend Collection Hotel
View all properties

Top Pittsfield Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"One of my favorite hotels in America - for real!"
Martha 2-night trip
Posted 2 days ago
Hotel On North
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 days ago
The Red Lion Inn
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"It was very nice and everyone was extremely helpful"
ERICIA 1-night trip
Posted 9 days ago
FairBridge Inn Express

Frequently asked questions

What's the best pet-friendly accommodation in Pittsfield?
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG is a top hotel for people traveling with their pets, and offers an indoor pool and a 24-hour fitness center for its human guests. Other good options for you and your pet's trip include Holiday Inn & Suites Pittsfield-Berkshires by IHG and Hotel On North.
How many hotels that welcome pets will I be able to find in Pittsfield?
Frolic with your furry friend at one of Expedia's 6 Pittsfield hotels that allow pets.
What's the best time of year to travel to Pittsfield with my pet?
When you travel with your pet, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to see and do with your pet in Pittsfield?
Known for its baseball and entertainment, Pittsfield has lots to offer visitors including its theaters, opera, and museums. See the local sights and visit Berkshire Museum and Colonial Theater. While you're there, make sure you don't miss Barrington Stage Company and Bousquet Ski Area.

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